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【结 构 式】

【分子编号】49230

【品名】6-methyl 1-phenyl 2-bromohexanedioate

【CA登记号】

【 分 子 式 】C13H15BrO4

【 分 子 量 】315.1637

【元素组成】C 49.54% H 4.8% Br 25.35% O 20.31%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XVII)

The reaction of adipic acid monomethyl ester (XIII) with SOCl2 gives the acyl chloride (XIV), which is brominated with NBS in carbon tetrachloride to yield 5-bromo-5-(chloroformyl)pentanoic acid methyl ester (XV). The reaction of (XV) with phenol (XVI) by means of DIEA in ethyl ether affords the mixed diester (XVII), which is reduced with tri-tert-butoxylithiumaluminum hydride in THF to provide 5-bromo-5-formylpentanoic acid methyl ester (XVIII). The cyclization of (XVIII) with chiral ethanone (XIX) by means of DIEA in hot dioxane gives the methyl ester (XX) of the target compound, which is finally hydrolyzed with NaOH in ethanol/water to obtain the target acid . The intermediate chiral ethanone (XIX) has been obtained as follows: The reaction of the chiral alcohol (VIII) with 4-hydroxybenzoic acid methyl ester (XXI) under Mitsunobu conditions (DEAD, PPh3) gives the chiral ether (XXII), which is then condensed with 2-methylpyridine (XXIII) by means of LiHMDS in THF to yield the target ethanone.

1 Sawada, K.; Tanaka, H.; Watanabe, S.; Kuroda, A.; Okada, S. (Fujisawa Pharmaceutical Co., Ltd.); Process for the preparation of indolizine derivs.. WO 9507279 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 49223 (1R)-1-(4-isobutylphenyl)-1-butanol C14H22O 详情 详情
(XIII) 49227 6-methoxy-6-oxohexanoic acid C7H12O4 详情 详情
(XIV) 49228 methyl 6-chloro-6-oxohexanoate C7H11ClO3 详情 详情
(XV) 49229 methyl 5-bromo-6-chloro-6-oxohexanoate C7H10BrClO3 详情 详情
(XVI) 23540 Phenol 108-95-2 C6H6O 详情 详情
(XVII) 49230 6-methyl 1-phenyl 2-bromohexanedioate C13H15BrO4 详情 详情
(XVIII) 49231 methyl 5-bromo-6-oxohexanoate C7H11BrO3 详情 详情
(XIX) 49232 1-(4-[[(1S)-1-(4-isobutylphenyl)butyl]oxy]phenyl)-2-(2-pyridinyl)-1-ethanone C27H31NO2 详情 详情
(XX) 49233 methyl 4-[1-(4-[[(1S)-1-(4-isobutylphenyl)butyl]oxy]benzoyl)-3-indolizinyl]butanoate C34H39NO4 详情 详情
(XXI) 10251 methyl 4-hydroxybenzoate; Methyl p-hydroxybenzoate 99-76-3 C8H8O3 详情 详情
(XXII) 49234 methyl 4-[[(1S)-1-(4-isobutylphenyl)butyl]oxy]benzoate C22H28O3 详情 详情
(XXIII) 17590 2-methylpyridine; 2-picoline 109-06-8 C6H7N 详情 详情
Extended Information